A self-taught artist, Olson spent his early years in Huntington, West Virginia. Orphaned at age 13, he enrolled at Fork Union Military Academy in Charlotte, North Carolina. After graduating, he went on to study at Marshall
College in Pennsylvania however was unable to complete his certificate due to financial hardships. After spending his savings, he moved to Alaska to work in the logging camps and would paint in his free time.
Finally, in 2003 Olson established himself on Shelter Island and has since honed his art practice and has exhibited regularly in local galleries and festivals.